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152633

Sigma-Aldrich

Olivetol

95%

Sinónimos:

1,3-Dihydroxy-5-pentylbenzene, 3,5-Dihydroxyamylbenzene, 5-Pentylresorcinol

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About This Item

Fórmula lineal:
CH3(CH2)4C6H3-1,3-(OH)2
Número de CAS:
500-66-3
Peso molecular:
180.24
EC Number:
207-908-8
MDL number:
MFCD00002293
UNSPSC Code:
12352100
PubChem Substance ID:
24849242
NACRES:
NA.22

Quality Level

200

assay

95%

form

solid

mp

46-48 °C (lit.)

SMILES string

CCCCCc1cc(O)cc(O)c1

InChI

1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3

InChI key

IRMPFYJSHJGOPE-UHFFFAOYSA-N

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Application

Olivetol was used as a template molecule in the synthesis of molecularly imprinted polymer (MIP). It was also used as an inhibitor of (S)-mephenytoin 4′-hydroxylase activity of recombinant CYP2C19.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 3 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1B - STOT SE 1 Oral - STOT SE 2 Oral

target_organs

Central nervous system,Blood, Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCK3927
MKCJ9089
MKCJ5839
MKCG1427
MKBZ9024V

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E A Formukong et al.
Inflammation, 12(4), 361-371 (1988-08-01)
Two extracts of Cannabis sativa herb, one being cannabinoid-free (ethanol) and the other containing the cannabinoids (petroleum), were shown to inhibit PBQ-induced writhing in mouse when given orally and also to antagonize tetradecanoylphorbol acetate (TPA)-induced erythema of mouse skin when
E A Formukong et al.
The Journal of pharmacy and pharmacology, 40(2), 132-134 (1988-02-01)
Tetrahydrocannabinol (THC) induced catalepsy in mice, whereas a cannabis oil (6.68% w/w THC), four cannabinoids and a synthetic mixture did not. Cannabinol (CBN) and olivetol inhibited THC-induced catalepsy in the mornings and the evenings, but cannabidiol (CBD) exhibited this effect
Lewis J Kearsey et al.
The FEBS journal, 287(8), 1511-1524 (2019-10-13)
In the native pathway to therapeutic cannabinoid biosynthesis in Cannabis sativa, the three-step production of a key intermediate, olivetolic acid, is catalysed by the enzymes tetraketide synthase (TKS; linear tetraketide intermediate production in two stages) and olivetolic acid cyclase (OAC; final
Analysis of olivetol in rabbit serum by high-performance liquid chromatography.
D Rauls et al.
Journal of chromatography, 234(2), 500-502 (1982-01-15)
M Fellermeier et al.
FEBS letters, 427(2), 283-285 (1998-06-02)
A new enzyme, geranylpyrophosphate:olivetolate geranyltransferase (GOT), the first enzyme in the biosynthesis of cannabinoids could be detected in extracts of young leaves of Cannabis sativa. The enzyme accepts geranylpyrophosphate (GPP) and to a lesser degree also nerylpyrophosphate (NPP) as a
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